Process of making 3-substituted-2-oxazolidinones



United States Patent PROCESS OF MAKING 3-SUBSTITU'IED-2- OXAZOLIDINONES Robert C. Harrington, Jr., Kingsport, Tenn., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application March 19, 1957 Serial No. 646,970

6 Claims. (Cl. 260-307) This invention relates to a novel 3-substituted-Z-oxazolidinones.

I have discovered that 3-substituted-2-oxazolidinones, in which the 3-substituent is phenyl, lower alkyl, or loweralkyl-substituted phenyl, can be prepared by heating the corresponding aryl, alkyl or alkaryl isocyanate with ethylene carbonate in the presence of a small amount of an alkaline or acid catalyst. For example, 3-phenyl-2-oxazoprocess of making lowing equation:

HQC CH: HQO -CHI CoHt.N:C O -s A) C0:

\ CoHs-N\ i i The catalysts which may be used include sodium carbonate, hydroxide, potassium hydroxide, zinc chloride, and stannous chloride. I prefer to use sodium carbonate. Moisture should be excluded from the reaction mixture.

By way of invention, I give the following examples.

Example ].-A mixture of 97 ethylene carbonate, 119

illustrating the method of carrying out my Patented Dec. 23, 1958 distilling under 3 mm. pressure. The fraction boiling at 165 C. was identified as 3-phenyl-2-oxazolidinone. It had a melting point of 118 ing point of 118 C. when mixed with 3-phenyl-2oxaz0- lidinone prepared by a known method. A yield of (based on phenyl isocyanate) of 3-phenyl-2-oxazolidinone was obtained from this reaction.

Among the other isocyanates which I may employ in the process of my invention, to give the corresponding 3-substituted-Z-oxazolidinones, are methyl isocyanate, ethyl isocyanate, tolyl isocyanate, and ethyl-phenyl isocyanate.

The 3-substituted-2-oxazolidinones are useful as solvents and plasticizers for cellulose esters and acrylic polymers.

What I claim as my invention and by Letters Patent 1. A process desire to be secured of the United States is: of making 3-phenyl-2-oxazolidinone of moisture, until reaction has taken place.

3. A process of making a 3-substituted-Z-oxazolidinone in which the 3-substituent is selected from the group consisting of phenyl, methyl, ethyl, tolyl, and ethylphenyl, which comprises heating the corresponding orand their salts with weak acids, in the absence of appremoisture, until reaction has taken amounts of moisture, until reaction has taken place.

5. A process of making 3-phenyl-2-oxazolidinone which comprises heating phenyl isocyanate with ethylene carbonate in the presence of an alkaline agent selected from the group consisting of alkali-forming metal compounds giving a hydroxyl ion and their salts with weak acids, in the absence of appreciable amounts of moisture, until reaction has taken place.

6. A process of making No references cited.

C., and gave a mixed melt- 

3. A PROCESS OF MAKING A 3-SUBSTITUTED-2-OXAZOLIDINONE IN WHICH THE 3-SUBSTITUENT IS SELECTED FROM THE GROUP CONSISTING OF PHENYL, METHYL, ETHYL, TOLYL, AND ETHYLPHENYL, WHICH COMPRISES HETING THE CORRESPONDING ORGANIC ISOCYANATE WITH ETHYLENE CARBONATE IN THE PRESENCE OF AN ALKALINE AGENT SELECTED FROM THE GROUP CONSISTING OF ALKALI-FORMING METAL COMPOUNDS GIVING A HYDROXYL ION AND THEIR SALTS WITH WEAK ACIDS, IN THE ABSENCE OF APPRECIABLE AMOUNTS OF MOISTURE, UNTIL REACTION HAS TAKEN PLACE.
 4. A PROCESS OF MAKING A 3-SUBSTITUTED-2-OXAZOLIDINONE, IN WHICH THE 3-SUBSTITUENT IS SELECTED FROM THE GROUP CONSISTING OF PHENYL, METHYL, ETHYL, TOLYL, AND ETHYL-PHENYL, WHICH COMPRISES HEATING THE CORRESPONDING ORGANIC ISOCYANATE WITH ETHYLENE CARBONATE IN THE PRESENCE OF AN ACIDIC CONDENSATION CATALYST, IN THE ABSENCE OF APPRECIABLE AMOUNTS OF MOISTURE, UNTIL REACTION HAS TAKEN PLACE. 